Synthesis and characterization of cationic iodonium macrocycles

Area of Science:

• Organic Chemistry
• Supramolecular Chemistry
• Materials Science

Background:

• Macrocyclic compounds are essential in various fields, including molecular recognition and materials science.
• Iodonium compounds are of interest for their unique electronic properties and potential applications in molecular electronics.

Purpose of the Study:

• To develop a high-yield synthetic strategy for novel iodonium-containing macrocycles.
• To explore the preparation of rhomboid, square, and pentagon-shaped iodonium macrocycles.
• To lay the groundwork for future applications of these compounds in molecular electronics.

Main Methods:

• Treatment of precursor compounds (11, 12a, 12b, dication 8, and compound 6) with trimethylsilyl trifluoromethanesulfonate (Me3SiOTf).
• Characterization of the synthesized iodonium-containing macromolecules using multinuclear Nuclear Magnetic Resonance (NMR) spectroscopy, mass spectrometry, and physical methods.

Main Results:

• Successful synthesis of two novel cationic rhomboid-shaped iodonium macrocycles in 55-70% yield.
• Preparation of an iodonium-containing molecular square in 70% yield.
• Synthesis of a pentagon-shaped iodonium macromolecule in 60% yield.

Conclusions:

• A versatile synthetic strategy for high-yield preparation of diverse iodonium-containing macrocycles has been established.
• The synthesized macrocycles represent a new class of charged macromolecules with potential for molecular electronics.
• Further investigation into the properties and applications of these iodonium macrocycles is warranted.